Abstract
A rapid method for selective cleavage of aryl methylethers can be achieved in the presence of a protic acid and a catalytic amount of phase-transfer catalyst (Aliquat-336). Aliquat-336 accelerates the rate of reaction and affords the corresponding phenols in excellent to good yields on a wide variety of substrates.
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GRAPHICAL ABSTRACT
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ACKNOWLEDGMENTS
S. B. W. and V. P. P. thank the Department of Science and Technology (DST), New Delhi, for financial support and the Council of Scientific and Industrial Research for a junior research fellowship, respectively.
Notes
Note. Reaction conditions: 2-methoxy naphthalene (20 mmol); 47% HBr (4.5 mmol equiv.); PTC (10 wt.% of substrate); temp. = 105 ± 5 °C; time = 2 h.
a Conversion based on GC analysis.
Note. Reaction conditions: 2-methoxy naphthalene (20 mmol); 47% HBr (4.5 mmol equiv.); Aliquat-336 (10 wt.% of substrate); time = 2 h.
a Conversion based on GC analysis.
Note. Reaction conditions: 2-methoxynaphthalene (20 mmol); 47% HBr (4.5 mmol equiv.); Aliquat-336 (10 wt.% of substrate); temp. = 105 ± 5 °C.
a Reaction conditions: Aryl methyl ether (10 mmol); 47% HBr (4.5 mmol equiv. of substrate); Aliquat-336 (10 wt.% of substrate); temp. = 105 ± 5 °C.
b Isolated yields.